Vacation Shoes

Jet-setting to your dream destination? Time to step up your shoe game with the ultimate collection of vacation shoes that’ll have you strutting like you own every runway from the airport terminal to the sandy shores. Whether you're chasing sunsets or city lights, these styles are all about turning heads and taking names. From beachy vibes to urban adventures, find the kicks that vibe with your wanderlust and make every step a stylish story. So, pack those bags and let your shoes do the talking—because life's too short for boring footwear!

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Windsor Tag Along Strappy Buckle Sandals in White

$9.97 $14.90 33% off

A pair of white strappy sandals featuring dual buckle straps and a comfortable flat sole.

Windsor Cutie Vibe Gingham Print Thong Strap Sandals in Blue

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Windsor Cutie Vibe Gingham Print Thong Strap Sandals in Blue

$9.97 $14.90 33% off

A cute gingham print thong strap sandal in blue faux leather perfect for spring and summer.

Sale

Everyday Chic Cutout Sandals in White

$9.97 $19.90 50% off

A chic pair of white faux leather slide sandals featuring an H-shaped band and square toe design.

Windsor Heart Eyes Only Slide Sandals in Clear

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Windsor Heart Eyes Only Slide Sandals in Clear

$9.97 $20.90 52% off

A clear PVC slide sandal featuring a bold heart charm and a comfortable platform footbed.

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Windsor Weekend Getaway Lace-Up Espadrille Wedges Shoes in Tan

$9.97 $36.90
73% off

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These chic espadrille wedges are the perfect excuse for a weekend getaway! They feature a trendy closed square toe and lace-up ankle straps that let you customize the look. Fit & FeaturesEspadrille wedge heel, Closed square toe, Lace-up ankle straps, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Weekend Getaway Lace-Up Espadrille Wedges Shoes in Tan | Size: 10

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Perfect Pair Bow Detail Thong Strap Sandals in Silver

$9.97 $14.90
33% off

(2)

The perfect pair of sandals for casual weekend plans! The thong strap design features a bow accent for the cutest detail. Fit & FeaturesFaux leather material, Almond-shaped toe, Thong strap design, bow detail, Open back, on-and-off styling, Flat sole, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Perfect Pair Bow Detail Thong Strap Sandals in Silver | Size: 8.5 | Leather

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On Vacay Flower Strap Jelly Sandals in Beige

$9.97 $14.90
33% off

(2)

These cute jelly sandals say "I'm on vacay" with the thong strap design and pretty flower accent. The open back offers effortless on-and-off styling. Fit & FeaturesJelly material, Open almond-shaped toe, Thong strap design, Flower accent, Open back, on-and-off styling, Flat sole, Runs true to size, Free Shipping on All Orders Over $75. | Windsor On Vacay Flower Strap Jelly Sandals in Beige | Size: 9

Sale

Windsor Tag Along Strappy Buckle Sandals in White

$9.97 $14.90
33% off

(1)

Whatever your summer plans are, these strappy buckle sandals are perfect for tagging along on any adventure! Fit & FeaturesRound toe, Dual buckle straps, Flat sole, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Tag Along Strappy Buckle Sandals in White | Size: 6

Sale

Windsor Such A Stud Strappy Jelly Sandals in Black

$9.97 $18.90
47% off

(1)

Put an edgy-cute foot forward in these jelly sandals with dual straps and studded accents that elevate your everyday look. Fit & FeaturesRound toe, Dual straps with studded accents, Flat sole, Jelly material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Such A Stud Strappy Jelly Sandals in Black | Size: 9

Chasing Sunshine Crochet Wedges Shoes in Beige

$45.90

(1)

These crochet wedge mules serve beachy vibes with an elevated twist, perfect for brunch, shower celebrations, or dinners al fresco. Fit & FeaturesSquare toe, Wide strap, Wedge sole, Crochet material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Chasing Sunshine Crochet Wedges Shoes in Beige | Size: 10

Sale

Windsor Cutie Vibe Gingham Print Thong Strap Sandals in Blue

$9.97 $14.90
33% off

(1)

You'll love the cute vibe these thong strap sandals bring to your weekend 'fits! The adorable gingham print is a spring and summer staple. Fit & FeaturesFaux leather material, Gingham print, Almond-shaped toe, Thong strap design, Open back, on-and-off styling, Flat sole, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Cutie Vibe Gingham Print Thong Strap Sandals in Blue | Size: 9 | Leather

Sale

Windsor Get It Girl Buckle Strappy Sandals in Black

$8.97 $20.90
57% off

(1)

Capture It-Girl vibes in these dual buckle strappy sandals perf for any of your casual plans! Fit & FeaturesSquare toe, Dual buckle adjustable straps, Luxe fit cushioned insole, Flat sole, Faux leather material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Get It Girl Buckle Strappy Sandals in Black | Size: 8.5 | Leather

Sale

Everyday Chic Cutout Sandals in White

$9.97 $19.90
50% off

Bringing effortless energy wherever you go. These chic slide sandals are your no-brainer pick for sun-soaked strolls, coffee runs, and last-minute plans. Fit & FeaturesSquare toe, H-shaped band, Flat sole, Faux leather material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Everyday Chic Cutout Sandals in White | Size: 10 | Leather

Sale

Playing It Cute Strappy Buckle Wedge Heels in White

$9.97 $26.90
63% off

Elevate your style with these irresistible strappy wedge heels featuring an eye-catching buckle accent. Fit & FeaturesWedge heel, Square toe, Strappy design, buckle accent, Faux leather material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Playing It Cute Strappy Buckle Wedge Heels in White | Size: 7 | Leather

Vacation Shoes

Vacations have a way of rewriting your daily dress code, and your shoes are often the first thing to catch up to that new rhythm. Whether you’re jetting off somewhere tropical in the thick of December or plotting a cozy winter escape, the right vacation shoes make all the difference between “barely made it” and “effortlessly arrived.” Think about it: every day on your trip is a new adventure—one moment you’re wandering cobblestone streets in a sun-soaked city, the next you’re dipping your toes in the pool or racing to catch a sunset dinner. Shoes that can keep up with all of that? Non-negotiable. The best vacation footwear is all about versatility, comfort, and a little bit of “throw them in your bag and go.” Supportive sneakers are a lifesaver for those long days spent exploring, giving you the arch support and cushioning you need to actually enjoy the journey (not just the destination). Lightweight sandals and slides are your answer to hot climates, water-side lounging, and impromptu strolls from the beach to brunch. And when you need something that can move seamlessly from casual afternoons to dressier evenings, packable flats or chic slip-ons have you covered—no extra suitcase required.

But vacation shoes aren’t just for the one wearing them. If you’re looking to gift someone a little piece of their next adventure, shoes windsor are a thoughtful and practical pick. They’re the kind of present that says, “I know you’ve got places to go—and I want you to get there in style.” For the friend who’s always planning her next city break, a pair that blends comfort and trend-forward details is guaranteed to land in her carry-on. For the sister who lives in sundresses and spontaneous road trips, breathable sandals or easy slides are a must. And if you’re shopping for yourself (because honestly, who knows your plans better than you?), windsor shoes make it easy to build a mini shoe wardrobe that works for every itinerary. Prioritize pairs that are lightweight and easy to pack, with enough support to keep you on your feet from sunrise explorations to late-night gelato runs. Closed-toe sneakers or boots are clutch for chillier, rainy destinations, while strappy sandals and airy flats are made for sun-drenched escapes.

Don’t underestimate the power of a shoe that can do double—or even triple—duty. The real secret to stress-free packing is choosing vacation shoes that can be dressed up or down, letting you move from daytime adventures to impromptu dinners without missing a beat. Look for pairs that are as stylish as they are functional, with details that elevate even the most casual outfit. And if your plans call for a little extra glam (because you never know when a rooftop invite might materialize), consider slipping a pair of dressier heels into your suitcase. For inspiration, check out the curated selection of Vacation Heels—perfect for those moments when you want to dial up the drama without sacrificing comfort. At the end of the day, the best vacation shoes should make you feel like you’re ready for anything. Whether you’re chasing new experiences or just soaking up the moment, Windsor has the styles to help you step confidently into every memory.

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